The present invention relates to a dye-forming coupler that forms an azomethine dye upon a coupling reaction with an oxidized product of a developing agent. The present invention also relates to a silver halide photographic light-sensitive material containing the dye-forming coupler. Further, the present invention relates to an azomethine dye compound that can be produced by the above-described coupling reaction.
In a silver halide photographic light-sensitive material (hereinafter sometimes referred to simply as xe2x80x9clight-sensitive materialxe2x80x9d) for subtractive color photography, a color image is formed by dyes of three primary colors of yellow, magenta and cyan. In the color photography that uses a current p-phenylenediamine color-developing agent, an acylacetoanilide-type compound is used as a yellow coupler. However, the hue of the yellow dye obtained from these yellow couplers is tinted with red, due to inferior sharpness at the foot portion of a peak in interest of the absorption curve at the longer wavelength side (that is, on the absorption curve, the peak in interest has subsidiary absorption at its foot portion at the longer wavelength side), which renders it difficult to obtain a yellow hue of high purity. Further, there is the problem that, due to the low molecular extinction coefficient of said yellow dyes, large amounts of both the coupler and silver halide are needed to obtain a desired colored density. Therefore, sometimes it results in increasing film thickness of the light-sensitive material, and this consequently reduces the sharpness of the obtained color image. Further, the above-mentioned yellow dyes, which are easily decomposed under the conditions of high temperature and high humidity, or the condition of light irradiation, have insufficient image stability after development processing. Consequently, improvement of these problems is desired.
In order to solve such the problems, the acyl group and the anilido group were improved. Recently, as improved couplers of the conventional acylacetoanilide-series, there are proposed, for example, 1-alkylcyclopropanecarbonyl acetoanilide-series compounds, described in JP-A-4-218042 (xe2x80x9cJP-Axe2x80x9d means unexamined published Japanese patent application); cyclomalonic acid diamide-type couplers, described in JP-A-5-11416; pyrrole-2- or 3-yl- or indole-2- or 3-yl-carbonylacetoanilide-series couplers, described in, for example, European Patent Nos. 953870A1, 953871A1, 953872A1, 953873A1, 953874A1 and 953875A1. The dyes formed from these couplers were improved in terms of both hue and molecular extinction coefficient, compared with the conventional ones. However, they are still deficient in image stability. Further, owing to their complicated chemical structure, the synthesis route became longer, and consequently cost of the couplers became higher, causing a practical problem.
In addition, U.S. Pat. No. 3,841,880, JP-A-52-82423 and JP-A-2-28645 propose acetate ester-series and acetoanilide-series couplers to which 1,2,4-benzothiadiazine-1,1-dioxide is bonded. However, these couplers are low in color-forming property, they are insufficient in molecular extinction coefficient of a resultant dye, and they are inferior in sharpness at the foot portion of a peak in interest of the absorption curve at the longer wavelength side. Therefore, improvement of these problems is desired.
Further, JP-A-58-111943 discloses a blocked magenta-dye-forming coupler. In JP-A-58-11943, there is described the magenta-dye-forming coupler which has a partial structure of acetanilide in which 1,2,4-benzothiadiazine-1,1-dioxide bonds to the blocking group of the coupler. However, said partial structure is just a blocking group. Since the blocking group moiety flows out from a light-sensitive material during development processing, the coupler having the partial structure is not used as an image dye.
Further, JP-A-4-78582 discloses a particular acetanilide-series azomethine dye, to which 1,2,4-benzothiadiazine-1,1-dioxide bonds, and which dye is used as a dye for a thermal transfer recording material. However, the dye is not satisfactory because of such problems that the image obtained from the dye is apt to be ambiguity and it is low in sharpness. In addition, neither fastness nor hue in view of sharpness at the foot portion of a peak in interest of the absorption curve at the longer wavelength side are sufficient.
The present invention is a dye-forming coupler represented by formula (I): 
wherein Q represents a group represented by xe2x80x94C(xe2x80x94R11)xe2x95x90C(xe2x80x94R12)xe2x80x94SO2xe2x80x94; R11 and R12 bond with each other to form, together with the xe2x80x94Cxe2x95x90Cxe2x80x94 moiety, a 5- to 7-membered ring, or R11 and R12 each independently represent a hydrogen atom or a substituent; R1 represents a substituent; R3 represents a substituent; R4 represents a substituent; m represents an integer of 0 to 4; when m is 2 or more, R4s may be the same or different, or R4s may bond each other to form a ring; and X represents a hydrogen atom, or a group capable of being split-off upon a coupling reaction with an oxidized product of a developing agent; with the proviso that the following compound (I-A) is excluded from the dye-forming coupler represented by formula (I). 
Further, the present invention is a dye-forming coupler represented by formula (II): 
wherein R1 represents a substituent; R2 represents a substituent; l represents an integer of 0 to 4; when l is 2 or more, R2s may be the same or different, or R2s may bond with each other to form a ring; R3 represents a substituent; R4 represents a substituent; m represents an integer of 0 to 4; when m is 2 or more, R4s may be the same or different, or R4s may bond with each other to form a ring; and Y represents a group capable of being split-off upon a coupling reaction with an oxidized product of a developing agent;
with the proviso that the following compound (I-A) is excluded from the dye-forming coupler represented by formula (I). 
Further, the present invention is a dye-forming coupler represented by formula (I-2): 
wherein Q1 represents a group represented by xe2x80x94C(xe2x80x94R11)xe2x95x90C(xe2x80x94R12)xe2x80x94Zxe2x80x94; Z represents xe2x80x94SO2xe2x80x94 or xe2x80x94COxe2x80x94; R11 and R12 bond with each other to form, together with the xe2x80x94Cxe2x95x90Cxe2x80x94 moiety, a 5- to 7-membered ring, or R11 and R12 each independently represent a hydrogen atom or a substituent; R1 represents a substituent; R3 represents a substituent; R4 represents a substituent; m represents an integer of 0 to 4; when m is 2 or more, R4s may be the same or different, or R4s may bond with each other to form a ring; and X1 represents a group that has thereon a dissociation group whose pKa is 1 to 12 and that is capable of being split-off upon a coupling reaction with an oxidized product of a developing agent.
Further, the present invention is a silver halide photographic light-sensitive material, which comprises at least one dye-forming coupler represented by the above formula (I), (II) or (I-2).
Further, the present invention is an azomethine dye compound represented by formula (D): 
wherein Q represents a group represented by xe2x80x94C(xe2x80x94R11)xe2x95x90C(xe2x80x94R12)xe2x80x94SO2xe2x80x94; R11 and R12 bond with each other to form, together with the xe2x80x94Cxe2x95x90Cxe2x80x94 moiety, a 5- to 7-membered ring, or R11 and R12 each independently represent a hydrogen atom or a substituent; R1 represents a substituent; R3 represents a substituent; R4 represents a substituent; m represents an integer of 0 to 4; when m is 2 or more, R4s may be the same or different, or R4s may bond with each other to form a ring; R5 and R6 each independently represent a hydrogen atom or a substituent, or R5 and R6 may bond with each other to form a ring; R7 represents a substituent; n represents an integer of 0 to 4; when n is 2 or more, R7s may be the same or different, or R7s may bond with each other to form a fused ring; or when n is 1 or more, R7 may bond with R5 or R6 to form a fused ring; with the proviso that at least one group selected from the group consisting of R1, R3, R4, the substituent represented by R11, the substituent represented by R12, and at least one substituent on the ring that is formed by a combination of R11 and R12, is a group having 10 or more carbon atoms in total.
Further, the present invention is an azomethine dye compound represented by formula (IV), wherein an angle that is defined by a dihedral angle C*1 N*2 C*3 C*4 and that is the most stabilized stereochemical structure in terms of energy, which is measured by quantum chemistry calculations, is within the range between xe2x88x9228xc2x0 and 28xc2x0: 
wherein, in formula (IV), *1, 2, *3 and 4 each express a number labeled on the atom and define the angle represented by the dihedral angle C*1 N*2 C*3 C*4; R3 and R4 each independently represent a substituent; m represents an integer of 0 to 4; when m is 2 or more, R4s may be the same or different, or R4s may bond with each other to form a ring; R5 and R6 each independently represent a hydrogen atom or a substituent, or R5 and R6 may bond with each other to form a ring; R8 represents an aryl group or a heterocyclic group,
with the proviso that at least one group selected from the group consisting of R3, R4, and at least one substituent on the aryl ring or heterocycle represented by R8, is a group having 10 or more carbon atoms in total; and that the calculation based on quantum chemistry, which is used to measure the dihedral angle C*1 N*2 C*3 C*4 be carried out using the basis function of 6-31 G** or more according to the widely used B3LYP method (density-functional method).
Further, the present invention is a silver halide photographic light-sensitive material, which comprises a coupler capable of forming a dye upon a coupling reaction with an oxidized product of an aromatic primary amine, wherein at least one dye to be formed is a dye selected from the azomethine dye compounds described above.
Other and further features and advantages of the invention will appear more fully from the following description.
According to the present invention, there is provided the following means:
(1) A dye-forming coupler represented by the following formula (I): 
xe2x80x83wherein Q represents a group represented by xe2x80x94C(xe2x80x94R11)xe2x95x90C(xe2x80x94R12)xe2x80x94SO2xe2x80x94 (in the present invention, this expression of the foregoing group should not be construed as limited to the direction of the bonds belonging to the group as represented by this expression); R11 and R12 bond with each other to form, together with the xe2x80x94Cxe2x95x90Cxe2x80x94 moiety, a 5- to 7-membered ring, or R11 and R12 each independently represent a hydrogen atom or a substituent; R1 represents a substituent; R3 represents a substituent; R4 represents a substituent; m represents an integer of 0 to 4; when m is 2 or more, R4s may be the same or different, or R4s may bond with each other to form a ring; and X represents a hydrogen atom, or a group capable of being split-off upon a coupling reaction with an oxidized product of a developing agent;
xe2x80x83with proviso that the following compound (I-A) is excluded from the dye-forming coupler represented by formula (I). 
(2) A dye-forming coupler represented by the following formula (II): 
xe2x80x83wherein R1 represents a substituent; R2 represents a substituent; l represents an integer of 0 to 4; when l is 2 or more, R2s may be the same or different, or R2s may bond with each other to form a ring; R3 represents a substituent; R4 represents a substituent; m represents an integer of 0 to 4; when m is 2 or more, R4s may be the same or different, or R4s may bond with each other to form a ring; and Y represents a group capable of being split-off upon a coupling reaction with an oxidized product of a developing agent;
xe2x80x83with the proviso that the following compound (I-A) is excluded from the dye-forming coupler represented by formula (II). 
(3) A dye-forming coupler represented by the following formula (I-2): 
xe2x80x83wherein Q1 represents a group represented by xe2x80x94C(xe2x80x94R11)xe2x95x90C(xe2x80x94R12)xe2x80x94Zxe2x80x94 (in the present invention, this expression of the foregoing group should not be construed as limited to the direction of the bonds belonging to the group as represented by this expression); Z represents xe2x80x94SO2xe2x80x94 or xe2x80x94COxe2x80x94; R11 and R12 bond with each other to form, together with the xe2x80x94Cxe2x95x90Cxe2x80x94 moiety, a 5- to 7-membered ring, or R11 and R12 each independently represent a hydrogen atom or a substituent; R1 represents a substituent; R3 represents a substituent; R4 represents a substituent; m represents an integer of 0 to 4; when m is 2 or more, R4s may be the same or different, or R4s may bond with each other to form a ring; and X1 represents a group that has thereon a dissociation group whose pKa is 1 to 12 and that is capable of being spilt-off upon a coupling reaction with an oxidized product of a developing agent.
(4) A dye-forming coupler represented by the following formula (II-2): 
xe2x80x83wherein R1 represents a substituent; R2 represents a substituent; l represents an integer of 0 to 4; when l is 2 or more, R2s may be the same or different, or R2s may bond with each other to form a ring; R3 represents a substituent; R4 represents a substituent; m represents an integer of 0 to 4; when m is 2 or more, R4s may be the same or different, or R4s may bond with each other to form a ring; and X1 represents a group that has thereon a dissociation group whose pKa is 1 to 12, and that is capable of being spilt-off upon a coupling reaction with an oxidized product of a developing agent.
(5) The dye-forming coupler according to any one of items (1) to (4), wherein R1 in said formula (I), (II), (I-2), or (II-2) is a substituted or unsubstituted alkyl group.
(6) The dye-forming coupler according to any one of items (1) to (5), wherein R3 in said formula (I), (II), (I-2), or (II-2) is a halogen atom, an alkoxy group, an aryloxy group, an alkyl group, an alkylthio group, or an arylthio group.
(7) The dye-forming coupler according to any one of items (1) to (6), wherein the substituent represented by R1 in said formula (I), (II), (I-2), or (II-2) has 11 or more carbon atoms in total.
(8) The dye-forming coupler according to any one of items (1) to (4), (6), and (7), wherein, in the above-mentioned formula (I), (II), (I-2) or (II-2), R1 represents a nondiffusible aliphatic group or aromatic group, and R3 represents a nondiffusible aliphatic oxy group or aromatic oxy group.
(9) The dye-forming coupler according to any one of items (1) to (8), wherein R1 in said formula (I), (II), (I-2), or (II-2) is a 3-(2,4-di-t-amylphenoxy)propyl group.
(10) The dye-forming coupler according to any one of items (1) to (8), wherein R1 in said formula (I), (II), (I-2), or (II-2) is a xe2x80x94C16H33 group or xe2x80x94C18H37 group.
(11) The dye-forming coupler according to any one of items (1) to (10), wherein X, X1 or Y in said formula (I), (II), (I-2), or (II-2) is a coupling-split-off group that substantially provides neither development inhibitor nor a precursor thereof, when the group splits off.
(12) The dye-forming coupler according to any one of items (1) to (11), wherein X, X1 or Y in the above-mentioned formula (I), (II), (I-2) or (II-2) is an imidazole-1-yl group which may have a substituent, a pyrazole-1-yl group which may have a substituent, or a pyrrole-1-yl group which may have a substituent.
(13) The dye-forming coupler according to any one of items (1) to (12), wherein R4 in the above-mentioned formula (I), (II), (I-2) or (II-2) is an alkoxy group or a t-alkyl group.
(14) The dye-forming coupler according to any one of items (1) to (7) and (9) to (13), wherein, in the above-mentioned formula (I), (II), (I-2) or (II-2), R3 represents an alkoxy group or alkylthio group, each of which has an alkyl moiety branched at the xcex2-position.
(15) The dye-forming coupler according to any one of items (1) to (14), wherein at least one of R1, R2, R3, R4, Q, Q1, X, X1 and Y in the above-mentioned formula (I), (II), (I-2) or (II-2) is a group containing therein a hydroxyl group.
(16) The dye-forming coupler according to any one of items (3) to (15), wherein the dissociation group that X1 of the above-mentioned formula (I-2) or (II-2) has is a group selected from the group consisting of a xe2x80x94COOH group, a xe2x80x94NHSO2xe2x80x94 group, a phenolic hydroxyl group, a xe2x80x94CONHCOxe2x80x94 group, a xe2x80x94CONHSO2xe2x80x94 group, a xe2x80x94CONHSO2NH2 group, and a xe2x80x94SO2NHSO2xe2x80x94 group, each of which has a pKa of 3 to 12.
(17) The dye-forming coupler according to any one of items (3) to (15), wherein the dissociation group that X1 of the above-mentioned formula (I-2) or (II-2) has is a xe2x80x94COOH group.
(18) A silver halide photographic light-sensitive material, comprising at least one dye-forming coupler according to any one of items (1) to (17).
(19) An azomethine dye compound represented by formula (D): 
xe2x80x83wherein Q represents a group represented by xe2x80x94C(xe2x80x94R11)xe2x95x90C(xe2x80x94R12)xe2x80x94SO2xe2x80x94 (in the present invention, this expression of the foregoing group should not be construed as limited to the direction of the bonds belonging to the group as represented by this expression); R11 and R12 bond with each other to form, together with the xe2x80x94Cxe2x95x90Cxe2x80x94 moiety, a 5- to 7-membered ring, or R11 and R12 each independently represent a hydrogen atom or a substituent; R1 represents a substituent; R3 represents a substituent; R4 represents a substituent; m represents an integer of 0 to 4; when m is 2 or more, R4s may be the same or different, or R4s may bond with each other to form a ring; R5 and R6 each independently represent a hydrogen atom or a substituent, or R5 and R6 may bond with each other to form a ring; R7 represents a substituent; n represents an integer of 0 to 4; when n is 2 or more, R7s may be the same or different, or R7s may bond with each other to form a fused ring; or when n is 1 or more, R7 may bond with R5 or R6 to form a fused ring;
xe2x80x83with the proviso that at least one group selected from the group consisting of R1, R3, R4, the substituent represented by R11 the substituent represented by R12, and at least one substituent on the ring that is formed by a combination of R11 and R12, is a group having 10 or more carbon atoms in total.
(20) An azomethine dye compound represented by the following formula (III): 
xe2x80x83wherein R1 represents a substituent; R2 represents a substituent; l represents an integer of 0 to 4; when l is 2 or more, R2s may be the same or different, or R2s may bond with each other to form a ring; R3 represents a substituent; R4 represents a substituent; m represents an integer of 0 to 4; when m is 2 or more, R4s may be the same or different, or R4s may bond with each other to form a ring; R5 and R6 each independently represent a hydrogen atom or a substituent, or R5 and R6 may bond with each other to form a ring; R7 represents a substituent; n represents an integer of 0 to 4; when n is the integer of 2 or more, R7s may be the same or different, or R7s may bond with each other to form a condensed ring; or when n is 1 or more, R7 may bond with R5 or R6 to form a condensed ring;
xe2x80x83with the proviso that at least one of the R1, R2, R3, or R4 is a group having 10 or more carbon atoms in total.
(21) The azomethine dye compound according to (19) or (20), wherein R1 in said formula (D) or (III) is a substituted or unsubstituted alkyl group.
(22) The azomethine dye compound according to any one of items (19) to (21), wherein R3 in said formula (D) or (III) is a halogen atom, an alkoxy group, an aryloxy group, an alkyl group, an alkylthio group, or an arylthio group.
(23) The azomethine dye compound according to any one of items (19) to (22), wherein the substituent represented by R1 in said formula (D) or (III) has 11 or more carbon atoms in total.
(24) The azomethine dye compound according to any one of items (19), (20), (22) or (23), wherein in the formula (D) or (III), R1 is a nondiffusible aliphatic group or aromatic group, and R3 is a nondiffusible aliphatic oxy group or aromatic oxy group.
(25) The azomethine dye compound according to any one of items (19) to (24), wherein R1 in said formula (D) or (III) is a 3-(2,4-di-t-amylphenoxy)propyl group.
(26) The azomethine dye compound according to any one of items (19) to (24), wherein R1 in said formula (D) or (III) is a xe2x80x94C16H33 group or xe2x80x94C18H37 group.
(27) An azomethine dye compound represented by the following formula (IV), wherein an angle that is defined by a dihedral angle C*1 N*2 C*3 C*4 and that is the most stabilized stereochemical structure in terms of energy, which is measured by quantum chemistry calculations, is within the range between xe2x88x9228xc2x0 and 28xc2x0: 
xe2x80x83wherein, in formula (IV), 1, 2, 3 and 4 each express a number labeled on the atom and define the angle represented by the dihedral angle C*1 N*2 C*3 C*4; R3 and R4 each independently represent a substituent; m represents an integer of 0 to 4; when m is 2 or more, R4s may be the same or different, or R4s may bond with each other to form a ring; R5 and R6 each independently represent a hydrogen atom or a substituent, or R5 and R6 may bond with each other to form a ring; R8 represents an aryl group or a heterocyclic group;
xe2x80x83with the proviso that at least one group selected from the group consisting of R3, R4, and at least one substituent on the aryl ring or heterocycle represented by R8, is a group having 10 or more carbon atoms in total; and that the quantum chemistry calculations, which is used to measure the dihedral angle C*1 N*2 C*3 C*4, be carried out using the basis function of 6-31 G** or more according to a widely used B3LYP method (density-functional method).
(28) The azomethine dye compound according to (27), wherein the angle defined by the dihedral angle C*1 N*2 C*3 C*4 of the most stabilized stereochemical structure in terms of energy, which is measured by quantum chemistry calculations, is within the range between xe2x88x9224xc2x0 and 24xc2x0.
(29) The azomethine dye compound according to (27) or (28), wherein R8 in said formula (IV) is a 6- or 7-membered heterocyclic group.
(30) The azomethine dye compound according to (27) or (28), wherein R8 in said formula (IV) is a group represented by the following formula (V): 
xe2x80x83wherein, in the formula (V), Q represents a group represented by xe2x80x94C(xe2x80x94R11)xe2x95x90C(xe2x80x94R12)xe2x80x94SO2xe2x80x94 (in the present invention, this expression of the foregoing group should not be construed as limited to the direction of the bonds belonging to the group as represented by this expression); R11 and R12 bond with each other to form, together with the xe2x80x94Cxe2x95x90Cxe2x80x94 moiety, a 5- to 7-membered ring, or R11 and R12 each independently represent a hydrogen atom or a substituent; and R1 represents a substituent.
(31) The azomethine dye compound according to (27) or (28), wherein R8 in said formula (IV) is a group represented by the following formula (VI): 
xe2x80x83wherein, in the formula (VI), R1 represents a substituent; R2 represents a substituent; and l represents an integer of 0 to 4; when l is 2 or more, R2s may be the same or different, or R2s may bond with each other to form a ring.
(32) The azomethine dye compound according to any one of items (27) to (31), wherein R3 in said formula (IV) is a halogen atom, an alkoxy group, an aryloxy group, an alkyl group, an alkylthio group, or an arylthio group.
(33) A silver halide photographic light-sensitive material, comprising a coupler capable of forming a dye upon coupling with an oxidized product of an aromatic primary amine, wherein at least one of said dyes is the azomethine dye compound according to any one of items (19) to (32).
(34) A silver halide photographic light-sensitive material, comprising a coupler capable of forming a dye upon coupling with an oxidized product of an aromatic primary amine, wherein at least one coupler is capable of giving the azomethine dye according to any one of items (19) or (32).
The present invention is explained in detail below.
(Dye-Forming Coupler)
The compound (herein also referred to as a dye-forming coupler) represented by the following formula (I) of the present invention is explained in detail. 
In formula (I), R1 represents a substituent excepting a hydrogen atom. Examples of the substituent include halogen atoms, alkyl (including cycloalkyl and bicycloalkyl), alkenyl (including cycloalkenyl and bicycloalkenyl), alkynyl, aryl, heterocyclic, cyano, hydroxyl, nitro, carboxyl, alkoxy, aryloxy, silyloxy, heterocyclic oxy, acyloxy, carbamoyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, amino (including alkylamino and anilino), acylamino, aminocarbonylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfamoylamino, alkyl- or aryl-sulfonylamino, mercapto, alkylthio, arylthio, heterocyclic thio, sulfamoyl, sulfo, alkyl- or aryl-sulfinyl, alkyl- or aryl-sulfonyl, acyl, aryloxycarbonyl, alkoxycarbonyl, carbamoyl, arylazo or heterocyclicazo, imido, phosphio, phosphinyl, phosphinyloxy, phosphinylamino, and silyl groups.
The above-mentioned substituent may be further substituted with another substituent. Examples of this another substituent are the same as described as the examples of the above-mentioned substituent.
Examples of the substituent represented by R1 are further explained below.
Examples of these substituents include a halogen atom (e.g., chlorine, bromine, iodine); an alkyl group (preferably a straight- or branched-chain, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, e.g., methyl, ethyl, n-propyl, isopropyl, t-butyl, n-octyl, eicosyl, 2-chloroethyl, 2-cyanoethyl, 2-ethylhexyl, and 3-(2,4-di-t-amylphenoxy)propyl); a cycloalkyl group (preferably a substituted or unsubstituted monocyclic cycloalkyl group having 3 to 30 carbon atoms, e.g., cyclohexyl, cyclopentyl, 4-n-dodecyl cyclohexyl; and polycyclic cycloalkyl groups including groups composed of a polycyclic structure, such as a bicycloalkyl group (preferably a substituted or unsubstituted bicycloalkyl group having 5 to 30 carbon atoms, e.g. bicyclo[1,2,2]heptane-2-yl and bicyclo[2,2,2]octane-3-yl), and a tricycloalkyl group; more preferably a monocyclic cycloalkyl group and a bicycloalkyl group, and particularly preferably a monocyclic cycloalkyl group); an alkenyl group (preferably a straight- or branched-chain, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, e.g., vinyl, allyl, prenyl, geranyl, oleyl); a cycloalkenyl group (preferably a substituted or unsubstituted monocyclic cycloalkenyl group having 3 to 30 carbon atoms, e.g., 2-cyclopentene-1-yl, 2-cyclohexene-1-yl; and a polycyclic cycloalkenyl group, such as a bicycloalkenyl group (preferably a substituted or unsubstituted bicycloalkenyl group having 5 to 30 carbon atoms, e.g., bicyclo[2,2,1]hepto-2-ene-1-yl and bicyclo[2,2,2]octo-2-ene-4-yl) and a tricycloalkenyl group, with a monocyclic cycloalkenyl group being particularly preferred); an alkynyl group (preferably a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, e.g., ethynyl, propargyl, trimethylsilylethynyl); an aryl group (preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, e.g., phenyl, p-tolyl, naphthyl, m-chlorophenyl, o-hexadecanoylaminophenyl); a heterocyclic group (preferably a 5- to 7-membered, substituted or unsubstituted, saturated or unsaturated, aromatic or non-aromatic, monocyclic or condensed heterocyclic group, more preferably a heterocyclic group having ring-constituting atoms selected from carbon, nitrogen and sulfur atoms, and containing at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur atoms, further preferably a 5- or 6-membered aromatic heterocyclic group having 3 to 30 carbon atoms, e.g., 2-furyl, 2-thienyl, 2-pyridyl, 4-pyridyl, 2-pyrimidinyl, 2-bemzothiazolyl); a cyano group; a hydroxyl group; a nitro group; a carbxyl group; an alkoxy group (preferably a substituted or unsubstituted alkoxyl group having 1 to 30 carbon atoms, e.g., methoxy, ethoxy, isopropoxy, t-butoxy, n-octyloxy, 2-methoxyethoxy); an aryloxy group (preferably a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, e.g., phenoxy, 2-methylphenoxy, 2,4-di-t-amylphenoxy, 4-t-buthylphenoxy, 3-nitrophenoxy, 2-tetradecanoylaminophenoxy); a silyloxy group (preferably a silyloxy group having 3 to 20 carbon atoms, e.g., trimethylsilyloxy, t-butyldimethylsilyloxy); a herocyclic oxy group (preferably a substituted or unsubstituted heterocyclic oxy group having 2 to 30 carbon atoms, more preferably having the same heterocycle moiety as that of the heterocyclic group, e.g., 1-phenyltetrazole-5-oxy, 2-tetrahydropyranyloxy); an acyloxy group (preferably formyloxy, a substituted or unsubstituted alkylcarbonyloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted arylcarbonyloxy group having 6 to 30 carbon atoms, e.g., formyloxy, acetyloxy, pivaloyloxy, stealoyloxy, benzoyloxy, p-methoxyphenylcarbonyloxy); a carbamoyloxy group (preferably a substituted or unsubstituted carbamoyloxy group having 1 to 30 carbon atoms, e.g., N,N-dimethylcarbamoyloxy, N,N-diethylcarbamoyloxy, morpholino carbonyloxy, N,N-di-n-octylaminocarbonyloxy, N-n-octylcarbamoyloxy); an alkoxycarbonyloxy group (preferably a substituted or unsubstituted alkoxycarbonyloxy group having 2 to 30 carbon atoms, e.g., methoxycarbonyloxy, ethoxycarbonyloxy, t-butoxy carbonyloxy, n-octylcarbonyloxy); an aryloxycarbonyloxy group (preferably a substituted or unsubstituted aryloxycarbonyloxy group having 7 to 30 carbon atoms, e.g., phenoxycarbonyloxy, p-methoxy phenoxycarbonyloxy, p-n-hexadecyloxyphenoxy carbonyloxy); an amino group (preferably an unsubstituted amino group, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, and a heterocyclic amino group having 0 to 30 carbon atoms, e.g., amino, methylamino, dimethylamino, anilino, N-methylanilino, diphenylamino, N-1,3,5-triazine-2-il amino), an acylamino group (preferably formylamino group, a substituted or unsubstituted alkylcarbonylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylcarbonylamino group having 6 to 30 carbon atoms, e.g., formylamino, acetylamino, pivaloylamino, lauroylamino, benzoylamino and 3,4,5-tri-n-octyloxyphenylcarbonylamino); an aminocarbonylamino group (preferably a substituted or unsubstituted aminocarbonylamino group having 1 to 30 carbon atoms, e.g., carbamoylamino, N,N-dimethylaminocarbonylamino, N,N-diethylamino carbonylamino, morpholinocarbonylamino), an alkoxycarbonylamino group (preferably a substituted or unsubstituted alkoxycarbonylamino group having 2 to 30 carbon atoms, e.g., methoxycarbonylamino, ethoxy carbonylamino, t-butoxycarbonylamino, n-octadecyloxycarbonylamino, N-methyl-methoxycarbonylamino); an aryloxycarbonylamino group (preferably a substituted or unsubstituted aryloxycarbonylamino group having 7 to 30 carbon atoms, e.g., phenoxycarbonylamino, p-chlorophenoxycarbonylamino, m-n-octyloxyphenoxycarbonyl amino); a sulfamoyl amino group (preferably a substituted or unsubstituted sulfamoylamino group having 0 to 30 carbon atoms, e.g., sulfamoylamino, N,N-dimethylaminosulfonylamino, N-n-octyl aminosulfonylamino); an alkyl- or aryl-sulfonylamino group (preferably a substituted or unsubstituted alkyl-sulfonylamino group having 1 to 30 carbon atoms, and a substituted or unsubstituted aryl-sulfonylamino group having 6 to 30 carbon atoms, e.g., methylsulfonylamino, butylsulfonylamino, phenylsulfonylamino, 2,3,5-trichlorophenylsulfonylamino, p-methylphenylsulfonylamino); a mercapto group; an alkylthio group (preferably a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, e.g., methylthio, ethylthio, n-hexadecylthio), an arylthio group (preferably a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, e.g., phenylthio, p-chlorophenylthio, m-methoxyphenylthio); a heterocyclic thio group (preferably a substituted or unsubstituted heterocyclic thio group having 2 to 30 carbon atoms in which the heterocycle moiety is preferably the same as that of the above-described heterocyclic group, e.g., 2-benzothiazolylthio, 1-phenyltetrazol-5-ylthio); a sulfamoyl group (preferably a substituted or unsubstituted sulfamoyl group having 0 to 30 carbon atoms, e.g., N-ethylsulfamoyl, N-(3-dodecyloxypropyl)sulfamoyl, N,N-dimethyl sulfamoyl, N-acetylsulfamoyl, N-benzoylsulfamoyl, Nxe2x80x94(Nxe2x80x2-phenylcarbamoyl) sulfamoyl); a sulfo group; an alkyl- or aryl-sulfinyl group (preferably a substituted or unsubstituted akylsulfinyl group having 1 to 30 carbon atoms, and a substituted or unsubstituted arylsulfinyl group having 6 to 30 carbon atoms, e.g., methyl sulfinyl, ethyl sulfinyl, phenylsulfinyl, p-methylphenylsulfinyl); an alkyl- or aryl-sulfonyl group (preferably a substituted or unsubstituted akyl sulfonyl group having 1 to 30 carbon atoms, and a substituted or unsubstituted arylsulfinyl group having 6 to 30 carbon atoms, e.g., methylsulfonyl, ethylsulfonyl, phenyl sulfonyl, p-methylphenylsulfonyl); an acyl group (preferably a formyl group, a substituted or unsubstituted alkylcarbonyl group having 2 to 30 carbon atoms, and a substituted or unsubstituted arylcarbonyl group having 7 to 30 carbon atoms, e.g., acetyl, pivaloyl, 2-chloroacetyl, stearoyl, benzoyl, p-n-octyloxyphenylcarbonyl); an aryloxycarbonyl group (preferably a substituted or unsubstituted aryloxycarbonyl group having 7 to 30 carbon atoms, e.g., phenoxycarbonyl, o-chlorophenoxycarbonyl, m-nitrophenoxy carbonyl, p-t-butylphenoxycarbonyl); an alkoxycarbonyl group (preferably a substituted or unsubstituted alkoxycarbonyl group having 2 to 30 carbon atoms, e.g., methoxycarbonyl, ethoxycarbonyl, t-butoxycarbonyl, n-octadecyloxycarbonyl); a carbamoyl group (preferably a substituted or unsubstituted carbamoyl group having 1 to 30 carbon atoms, e.g., carbamoyl, N-methylcarbamoyl, N,N-dimethylcarbamoyl, N,N-di-n-octylcarbamoyl, N-(methylsulfonyl)carbamoyl); an aryl azo group or heterocyclic azo group (preferably a substituted or unsubstituted aryl azo group having 6 to 30 carbon atoms, and a substituted or unsubstituted heterocyclic azo group having 3 to 30 carbon atoms, in which the heterocyclic moiety is preferably the same as that of the above-described heterocyclic group, e.g., phenylazo, p-chlorophenylazo, 5-ethylthio-1,3,4-thiadiazole-2-yl azo); an imido group (preferably a substituted or unsubstituted imido group having 2 to 30 carbon atoms, e.g., N-succinimido, N-phthalimido); a phosphino group (preferably a substituted or unsubstituted phosphino group having 2 to 30 carbon atoms, e.g., dimethylphosphino, diphenylphosphino, methylphenoxyphosphino); a phosphinyl group (preferably a substituted or unsubstituted phosphinyl group having 2 to 30 carbon atoms, e.g., phosphinyl, dioctyloxyphosphinyl, diethoxyphosphinyl); a phosphinyloxy group (preferably a substituted or unsubstituted phosphinyloxy group having 2 to 30 carbon atoms, e.g., diphenoxyphosphinyloxy, dioctloxyphosphinyloxy); a phosphinylamino group (preferably a substituted or unsubstituted phosphinylamino group having 2 to 30 carbon atoms, e.g., dimethoxyphosphinylamino, dimethylamino phosphinylamino); and a silyl group (preferably a substituted or unsubstituted silyl group having 3 to 30 carbon atoms, e.g., trimethylsilyl, t-butyl dimethylsilyl, phenyldimethylsilyl).
Among the above-described functional groups, a hydrogen atom(s) possessed in the functional group may be removed to replace with any one of the above-described groups. Examples of these functional groups include an alkylcarbonylaminosulfonyl group, an arylcarbonylaminosulfonyl group, an alkylsulfonylaminocarbonyl group, and an arylsulfonyl aminocarbonyl group. As the specific examples, methylsulfonyl aminocarbonyl, p-methylphenylsulfonylaminocarbonyl, acetylaminosulfonyl, and benzoylaminosulfonyl groups are enumerated.
R1 is preferably a substituted or unsubstituted alkyl group, more preferably a substituted alkyl group. As the substituent of the substituted alkyl group, those enumerated as the substituent of R1 mentioned above are exemplified. A total carbon atoms of R1 is preferably 1 to 60, more preferably 6 to 50, still more preferably 11 to 45, further more preferably 12 to 40, and most preferably 16 to 30.
R1 is preferably an alkyl group substituted with an alkoxy group or aryloxy group at the 2-, 3- or 4-position, more preferably an alkyl group substituted with an alkoxy group or aryloxy group at the 3-position, most preferably 3-(2,4-di-t-amylphenoxy)propyl group. As the unsubstituted alkyl group, a xe2x80x94C16H33 or xe2x80x94C18H37 group is preferred. In case where R1 is a xe2x80x94C16H33 or xe2x80x94C18H37 group, there is a merit that a coupler can be economically produced because C16H33NH2 and C18H37NH2, each of which is a raw material, are inexpensive.
In formula (I), Q represents a group represented by xe2x80x94C(xe2x80x94R11)xe2x95x90C(xe2x80x94R12)xe2x80x94SO2xe2x80x94 (in the present invention, this expression of the foregoing group should not be construed as limited to the direction of the bonds belonging to the group as represented by this expression). R11 and R12 collectively represent a group which forms a 5- to 7-membered ring, together with the xe2x80x94Cxe2x95x90Cxe2x80x94 moiety, when R11 and R12 bond with each other, or alternatively R11 and R12 each independently represent a hydrogen atom or a substituent. The 5- to 7-membered ring thus formed may be saturated or unsaturated, and the unsaturated ring may be an alicyclic, aromatic or heterocyclic ring. Examples of these rings include benzene, furan, thiophene, cyclopentene, and cyclohexane rings. Further, examples of the substituent represented by R11 and R12 are those enumerated as the substituent of the above-described R1.
Each of these substituents, or the ring which is formed by binding two or more kinds of substituents with each other, may be further substituted with a substituent as enumerated as the substituent of the above-described R1.
In formula (I), R3 represents a substituent except for a hydrogen atom. Examples of the substituent include those enumerated as the substituent of the above-described R1. R3 is preferably a halogen atom (e.g., fluorine, chlorine, bromine), an alkyl group (e.g., methyl, isopropyl), an alkoxy group (e.g., methoxy, isopropoxy), an aryloxy group (e.g., phenoxy, o-(2-ethylhexyloxy)phenoxy), an amino group (e.g., dimethylamino, morpholino), an acylamino group (e.g., acetoamido), and an sulfonamido group (e.g., methanesulfonamido, benzenesulfonamido), an alkylthio group (e.g. methylthio, isopropylthio, dodecylthio), an arylthio group (e.g. phenylthio, o-dodecyloxyphenylthio), more preferably a halogen atom, an alkoxy group, an aryloxy group, an alkyl group, an alkylthio group, and an arylthio group, and most preferably a fluorine atom, a chrorine atom, an alkoxy group, an aryloxy group, an alkylthio group, and an arylthio group.
As the alkoxy group and the alkylthio group, both branched alkoxy and alkylthio groups are preferred. The position of branch is preferably an xcex1-position or a xcex2-position, more preferably a xcex2-position.
As the aryloxy group and the arylthio group, preferred are those having a substituent at the ortho-position. Examples of the substituent are those enumerated as the substituent of the above-mentioned R1.
An aryloxy group and an arylthio group each having an alkyl group, an alkoxy group, or an alkylthio group at the ortho-position, are more preferred.
In formula (I), it is preferable that R1 is a nondiffusible aliphatic group or aromatic group, and R3 is a nondiffusible aliphatic oxy group or aromatic oxy group. As the nondiffusible aliphatic group, preferred are straight chain or branched alkyl groups having 7 to 30 carbon atoms, such as benzyl, octyl, 2-ethylhexyl, isotridecyl, hexadecyl, octadecyl, tetradecyl and dodecyl groups. As the nondiffusion aliphatic oxy group, preferred are straight chain or branched alkoxy groups having 7 to 30 carbon atoms, such as benzyloxy, octyloxy, 2-ethylhexyloxy, isotridecyloxy, hexadecyloxy, octadecyloxy, tetradecyloxy and dodecyloxy groups. Further, the alkyl moiety of the nondiffusible alkyl group represented by R1 and the nondiffusible alkoxy group represented by R3, may have a structure containing therein such a functional group as represented by the following formula (A):
formula (A)
xe2x80x94J1xe2x80x94J2xe2x80x94R10 
In formula (A), J1 represents a straight chain or branched alkylene group having 1 to 20 carbon atoms, such as methylene, 1,2-ethylene, 1,1-dimethylmethyle and 1-decylmethylene groups. R10 represents a straight chain or branched alkyl group having 1 to 20 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, 2-ethylhexyl and dodecyl groups. J2 represents a divalent linking group with preferred examples of xe2x80x94Oxe2x80x94, xe2x80x94OCOxe2x80x94, xe2x80x94OSO2xe2x80x94, xe2x80x94COxe2x80x94, xe2x80x94COOxe2x80x94, xe2x80x94CON(R121)xe2x80x94, xe2x80x94CON(R121)SO2xe2x80x94, xe2x80x94N(R121)xe2x80x94, xe2x80x94N(R121)COxe2x80x94, xe2x80x94N(R121)SO2xe2x80x94, xe2x80x94N(R121)CON(R122)xe2x80x94, xe2x80x94N(R121)COOxe2x80x94, xe2x80x94S(O)nxe2x80x94 and xe2x80x94S(O)nN(R121)xe2x80x94, in which R121 and R122 each represent a hydrogen atom, or those having the same meanings as the alkyl group and the aryl group represented by R1 in formula (I), and n represents an integer of 0 to 2. R10 and J1 may bond with each other to form a ring.
As the nondiffusible aromatic group represented by R1, preferred are aryl groups having 7 to 30 carbon atoms. The aryl group may have a substituent, such as those enumerated as the substituent of the above-mentioned R1.
As the nondiffusible aromatic oxy group represented by R3, preferred are aryloxy groups having 7 to 30 carbon atoms. The aryloxy groups may have a substituent such as those enumerated as the substituent of the above-mentioned R1.
In formula (I), R4 represents a substituent. Examples of the substituent include those enumerated as the substituent of the above-described R1. R4 is preferably a halogen atom, an alkyl group, an alkoxy group, an aryloxy group, an alkoxycarbonyl group, an aryloxycarbonyl group, a cabamoyl group, a sulfamoyl group, an acylamino group, an alkyl- or aryl-sulfonylamino group, an alkylthio group, and an arylthio group. m represents an integer of 0 to 4. When m is an integer of 2 or more, R4s may be the same or different, or R4s may bond with each other to form a ring.
More preferably, R4 is an alkyl group, an alkoxy group, an aryloxy group, an alkylthio group, or an arylthio group. More preferably, R4 is an alkyl group, or an alkoxy group. Most preferably, R4 is a t-alkyl group.
A substituted position of R4 is preferably para-position against a xe2x80x94CONHxe2x80x94 group, or para-position against R3, more preferably, R4 is para-position against R3.
In formula (I), X represents a hydrogen atom, or a group that can be split-off upon a coupling reaction with an oxidized product of a developing agent. Examples of the above-described group capable of being split-off upon a coupling reaction with an oxidized product of a developing agent include a group capable of being split-off with a nitrogen, oxygen, or sulfur atom (a splitting-off atom), and a halogen atom (e.g., chlorine, bromine).
Examples of the group that splits off with a nitrogen atom include a heterocyclic group (preferably 5-to 7-membered substituted or unsubstituted saturated or unsaturated aromatic (herein the term xe2x80x9caromaticxe2x80x9d is used to embrace a substance that has (4n+2) cyclic conjugated electrons) or non-aromatic, monocyclic or condensed heterocyclic groups, more preferably 5- or 6-membered heterocyclic groups, in which the ring-forming atoms are selected from carbon, nitrogen and sulfur atoms and in addition at least one of hetero atoms selected from nitrogen, oxygen and sulfur atoms is incorporated, with specific examples of the heterocyclic ring including succinimide, maleinimide, phthalimide, diglycolimide, pyrrole, pyrazole, imidazole, 1,2,4-triazole, tetrazole, indole, benzopyrazole, benzimidazole, benzotriazole, imidazoline-2,4-dione, oxazolidine-2,4-dione, thiazolidine-2-one, benzimidazoline-2-one, benzoxazoline-2-one, benzothiazoline-2-one, 2-pyrroline-5-one, 2-imidazoline-5-one, indoline-2,3-dione, 2,6-dioxypurine, parabanic acid, 1,2,4-triazolidine-3,5-dione, 2-pyridone, 4-pyridone, 2-pyrimidone, 6-pyridazone, 2-pyrazone, 2-amino-1,3,4-thiazolidine-4-one), a carbonamido group (e.g., acetamido, trifluoroacetamido), a sulfonamido group (e.g., methanesulfonamido, benzenesulfonamido), an arylazo group (e.g., phenylazo, naphthylazo), and a carbamoylamino group (e.g., N-methyl carbamoylamino).
Preferred of the group that splits off with a nitrogen atom are heterocyclic groups, more preferably aromatic heterocyclic groups having 1, 2, 3 or 4 ring-forming nitrogen atoms, or heterocyclic groups represented by the following formula (L). The heterocyclic groups represented by the following formula (L) are further more preferred: 
wherein L represents a moiety that forms a 5- to 6-membered nitrogen-containing heterocycle with xe2x80x94NC (xe2x95x90O)xe2x80x94.
Examples of the moieties are enumerated in the explanation of the above-mentioned heterocyclic group, and such moieties as enumerated above are more preferred. Particularly preferably L is a moiety that forms a 5-membered nitrogen-containing heterocyclic ring.
Examples of the group that splits off with an oxygen atom include an aryloxy group (e.g., phenoxy, 1-naphthoxy), a heterocyclic oxy group (e.g., pyridyloxy, pyrazolyloxy), an acyloxy group (e.g., acetoxy, benzoyloxy), an alkoxy group (e.g., methoxy, dodecyloxy), a carbamoyloxy group (e.g., N,N-diethylcarbamoyloxy, morpholinocarbamoyloxy), an aryloxycarbonyloxy group (e.g., phenoxycarbonyloxy), an alkoxycarbonyloxy group (e.g., methoxycarbonyloxy, ethoxycarbonyloxy), an alkylsulfonyloxy group (e.g., methanesulfonyloxy), and an aryl sulfonyloxy group (e.g., benzenesulfonyloxy, toluenesulfonyloxy).
Preferred of these groups capable of being spilt-off at the moiety of oxygen atom are an aryloxy group, an acyloxy group and a heterocyclic oxy group.
Examples of the group that splits off with a sulfur atom include an arylthio group (e.g., phenylthio, naphthylthio), a heterocyclic thio group (e.g., tetrazolylthio, 1,3,4-thiadiazolylthio, 1,3,4-oxazolylthio, benzimidazolyl thio), an alkylthio group (e.g., methylthio, octylthio, hexadecylthio), an alkylsulfinyl group (e.g., methane sulfinyl), an arylsulfinyl group (e.g., benzenesulfinyl), an arylsulfonyl group (e.g., benzenesulfonyl), and an alkylsulfonyl group (e.g., methansulfonyl).
Preferred of the group that splits off with a sulfur atom are an arylthio group and a heterocyclic thio group. A heterocyclic thio group is more preferred.
As X, a group that can be spilt-off upon a coupling reaction with an oxidized product of a developing agent is more preferred than a hydrogen atom. The above-said coupling spilt-off group may be substituted with a substituent such as those enumerated as the substituent of the above-mentioned R1.
X is preferably a group that can be spilt-off with a nitrogen or oxygen atom (a cleavable group), more preferably a group that can be spilt-off with a nitrogen atom. Further, those groups described as the preferable examples of the group that can be spilt-off with a nitrogen atom, are preferred in the same order as mentioned above.
X is more preferably a pyrazole-1-yl group, imidazole-1-yl group, pyrrole-1-yl group, each of which may have a substituent, or a heterocyclic group represented by the above-mentioned formula (L). X is more preferably a pyrazole-1-yl group, imidazole-1-yl group, pyrrole-1-yl group, each of which may have a substituent, most preferably an imidazole-1-yl group, or pyrrole-1-yl group, each of which may have a substituent.
X is preferably a group that gives substantially no development inhibitor, after X is spilt-off upon a coupling reaction with an oxidized product of a developing agent. The group X that releases a development inhibitor has a problem that the raw stock stability of an unexposed light-sensitive material is low due to the released development inhibitor. Examples of the group that releases a development inhibitor include a benzotriazole-1-yl, or -2-yl group, an arylthio group and a heterocyclic thio group.
Further, X is preferably a group that releases no magenta coupler, after X cleaved off upon a coupling reaction with an oxidized product of a developing agent. The group X that releases a magenta coupler, has a problem that a magenta dye and a yellow dye are present in a mixture after processing, resulting in a law color purity. Examples of the groups that release a magenta coupler after splitting, include a pyrazolo [5,1-b] [1,2,4] triazole-1-yl group a pyrazolo [1,5-b] [1,2,4] triazole-1-yl group, an indazolone-1-yl group, and a pyrazolo [1,5-a] benzimidazole-4-yl group, each of which may have a substituent.
Further, in case where 1,2,4-benzothiadiazine-1,1-dioxide ring is formed by Q, and/or in case where R1 is a methyl group, R3 is a chlorine atom and m is 0, a group that is cleavable upon a coupling reaction with an oxidized product of a developing agent, is more preferred than a hydrogen atom from the viewpoint of the effects which is obtained by the present invention.
In order to render the coupler inmobile in a light-sensitive material, at least one of Q, R1, X, R3 and R4 has preferably 7 to 50 carbon atoms, more preferably 10 to 50 carbon atoms, further preferably 10 to 40 carbon atoms, most preferably 12 to 35 carbon atoms, in total respectively, including carbon atoms of a substituent(s) that they may have thereon.
From the viewpoint of color-forming property, at least one of Q, R1, X, R3 and R4 is preferably a group containing therein a hydroxyl group, or a dissociation group whose pKa is 3 to 12 (e.g., a xe2x80x94COOH group, a xe2x80x94NHSO2-group, a phenolic hydroxyl group, a xe2x80x94CONHCOxe2x80x94 group, a xe2x80x94CONHSO2xe2x80x94 group, a xe2x80x94CONHSO2NH2 group, and a xe2x80x94SO2NHSO2-group). More preferably X is a group carrying therein the above-mentioned group(s).
Next, the compound represented by formula (I-2) according to the present invention (herein also referred to as a dye-forming coupler) is explained in detail. 
In formula (I-2), R1, R3, R4, and m each have the same meanings as those described in formula (I). Preferable examples of them are the same as described therein.
In formula (I-2), Q1 represents a group represented by xe2x80x94C(xe2x80x94R11)xe2x95x90C(xe2x80x94R12)xe2x80x94Zxe2x80x94 (in the present invention, this expression of the foregoing group should not be construed as limited to the direction of the bonds belonging to the group as represented by this expression). z represents SO2 or CO. R11 and R12, combined with each other, collectively represent a group that, together with the xe2x80x94Cxe2x95x90Cxe2x80x94 moiety, forms a 5- to 7-membered ring, or R11 and R12 each independently represent a hydrogen atom or a substituent. The 5- to 7-membered ring that is formed by a combination of R11 and R12 may be a saturated or unsaturated alicyclic, aromatic or heterocyclic ring, such as benzene, furan, thiophene, cyclopentane and cyclohexane rings. In case where R11 and R12 represent a substituent, examples of the substituent are those enumerated as the substituent of the above-mentioned R1.
In formula (I-2), X1 is a group that has therein a dissociation group having pKa of 1 to 12, and that is capable of being spilt-off upon a coupling reaction with an oxidized product of a developing agent. Examples of the group that can be spilt-off upon a coupling reaction with an oxidized product of a developing agent, are the same as those of the coupling-spilt-off group of X in formula (I). Preferable examples of the group are also common to those of X. However, it is necessary in formula (I-2) that these coupling-cleavable groups further carry therein a dissociation group having pKa of 1 to 12. Said dissociation groups are explained below.
The pKa of the dissociation group carried in X1 preferably ranges from 1 to 12, more preferably from 3 to 12. Preferable examples of the dissociation group include a xe2x80x94COOH group, a xe2x80x94NHSO2xe2x80x94 group, a phenolic hydroxyl group, a xe2x80x94CONHCOxe2x80x94 group, a xe2x80x94CONHSO2xe2x80x94 group, a xe2x80x94CONHSO2NH2xe2x80x94 group and a xe2x80x94SO2NHSO2xe2x80x94 group. It is more preferably a xe2x80x94COOH group, a xe2x80x94NHSO2xe2x80x94 group or a xe2x80x94CONHSO2xe2x80x94 group, and most preferably a xe2x80x94COOH group.
The number of dissociation groups is at least 1 as a necessity, preferably from 1 to 2, more preferably 1.
Next, the compound represented by formula (II) according to the present invention (herein also referred to as a dye-forming coupler) is explained in detail. 
In formula (II), R1, R3, R4, and m each have the same meanings as those described in formula (I). Preferable examples of them are the same as described therein.
In formula (II), R2 represents a substituent. Examples of the substituent include those enumerated as the substituent of R1 described above. l represents an integer of 0 to 4. When l is 2 or more, R2s may be the same or different, or R2s may bond with each other to form a ring.
In formula (II), Y represents a group capable of being split-off upon a coupling reaction with an oxidized product of a developing agent. Examples of Y include those enumerated as the examples of X being a group capable of being split-off upon a coupling reaction with an oxidized product of a developing agent. Preferable examples of Y are the same as those of X.
Among the couplers represented by the formula (II), further preferable couplers include:
1) Couplers wherein R1 represents an alkyl group, Y represents an imidazole-1-yl group which may have a substituent or a pyrrole-1-yl group which may have a substituent (preferably an imidazole-1-yl group which may have a substituent), R3 represents an alkoxy group, m is 1 to 2 (preferably 1), and R4 represents a substituent, in which at least one of R4 is a group selected from an alkyl group, a cycloalkyl group or an alkoxy carbonyl group and substituted at a para-position relative to R3; or
2) Couplers wherein R1 represents an alkyl group, Y represents a group represented by the formula (L), R3 represents an alkoxy group, an aryloxy group, an alkyl thio group or an aryl thio group, m is 1 to 2 (preferably 1) and R4 represents a substituent, in which at least one of R4 is substituted at a para-position relative to R3.
Both 1) and 2) are those wherein R2 and 1 are as defined in the formula (II), and preferably both 1) and 2) are those wherein 1 is 0. Further, the respective groups described above are more preferable in the order of the description of the groups mentioned to be preferable.
Among the couplers in 1) above, further preferable couplers can be represented by the following formula (IIA). The couplers represented by the formula (IIA) are further preferable in respect of color-forming property and hue of the resultant dye. 
In the formula (IIA), R11 and R12 each independently represent a substituted or unsubstituted alkyl group. R13 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted alkoxy carbonyl group. R14, R15 and R16 each independently represent a hydrogen atom or a substituent. R17 represents a substituent. p represents an integer of 0 to 3. When p is 2 to 3, a plurality of R17 groups may be the same or different.
Among the couplers represented by the formula (IIA), the couplers represented by the following formula (IIB) are preferable in respect of excellent color-forming property, even when the coupling reaction with an oxidized product of a developing agent is conducted under the condition of relatively high pH. 
In the formula (IIB), R21 and R22 each independently represent a substituted or unsubstituted alkyl group. R23 represents an unsubstituted alkyl group or an unsubstituted cycloalkyl group. R24, R25 and R26 each independently represent a hydrogen atom, a chlorine atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted alkoxy carbonyl group. R27 represents a substituted or unsubstituted alkyl group, a halogen atom, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted alkylamino carbonyl group. p represents an integer of 0 to 3. When p is 2 or 3, a plurality of R27 groups may be the same or different.
The couplers represented by the formula (IIB) are described in more detail.
R21 is preferably a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms (for example, methyl, ethyl, n-propyl, isopropyl, octadecyl). R21 is more preferably an unsubstituted alkyl group having 1 to 30 carbon atoms, further preferably an unsubstituted alkyl group having 12 to 20 carbon atoms. R21 is most preferably n-octadecyl.
R22 is preferably a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms (for example, methyl, ethyl, n-propyl, n-butyl). R22 is more preferably an unsubstituted alkyl group having 1 to 6 carbon atoms. R22 is most preferably methyl, ethyl or n-propyl.
R23 is preferably an unsubstituted alkyl group having 1 to 20 carbon atoms (for example, methyl, ethyl, t-butyl, 1,1,3,3-tetramethylbutyl). R23 is more preferably an alkyl group having 4 to 8 carbon atoms. R23 is most preferably t-butyl.
Preferably, R24 and R25 each independently represent a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, and an alkoxy carbonyl group having 2 to 20 carbon atoms which may have a substituent (preferably an unsubstituted alkoxy carbonyl group). More preferably, R24 and R25 each independently represent a hydrogen atom, methoxycarbonyl and ethoxycarbonyl.
R26 is preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R26 is most preferably a hydrogen atom.
R27 is preferably an unsubstituted alkyl group having 1 to 20 carbon atoms, a halogen atom, an unsubstituted alkoxy group having 1 to 20 carbon atoms.
p is preferably 0 or 1. p is more preferably 0.
The most preferable structure of the coupler represented by the formula (IIB) is a coupler wherein R21 is an unsubstituted alkyl group having 12 to 20 carbon atoms, R22 is an unsaturated alkyl group having 1 to 6 carbon atoms, R23 is an unsubstituted alkyl group having 4 to 8 carbon atoms, R24 and R25 each independently represent a hydrogen atom, a methoxy carbonyl group or an ethoxy carbonyl group, R26 is a hydrogen atom, and p is 0.
Next, the compound represented by formula (II-2) according to the present invention (herein also referred to as a dye-forming coupler) is explained in detail. 
In formula (II-2), R1, R2, R3, R4, l, m, and X1 each have the same meanings as those described in formula (I), (II) or (I-2). Preferable examples of them are the same as described therein.
Preferable combinations of the groups (substituents) having bonded to the coupler represented by formula (I), (II), (I-2) or (II-2) according to the present invention are explained below. That is, R1 is a 3-(2,4-di-t-amylphenoxy) propyl group, a xe2x80x94C16H33 group, or a xe2x80x94C18H37 group; R3 is a halogen atom, an alkoxy group, an aryloxy group, an alkylthio group, or an arylthio group, and X, Y, and X1 are each independently a heterocyclic group represented by the above-mentioned formula (L), or a pyrazole-1-yl group, imidazole-1-yl group, or pyrrole-1-yl group, each of which may have a substituent.
In the present invention, the compound (I-A) described below is excluded from the couplers represented by formula (I) or (II). Said compound (I-A) is a blocked magenta coupler. The acetanilide moiety which bonds with 1,2,4-benzothiadiazine-1,1-dioxide, is just a blocking group, which flows out from a light-sensitive material after development processing, so that the acetanilide moiety is not used as an image dye. Even though this blocking group of the acetanilide moiety does not flow out from the light-sensitive material, a yellow dye and a magenta dye are present in a mixture, so that the intended effects of the present invention cannot be exhibited. 
The coupler of the present invention is preferably useful as a yellow dye-forming coupler or a magenta dye-forming coupler, although according to a developing agent used in a coupling reaction. Especially, it is useful as a yellow dye-forming coupler. Additionally, a maximum absorption wavelength of the obtained dye is generally 400 to 500 nm, preferably 410 to 480 nm, and more preferably 420 to 460 nm.
Preferable specific examples of the couplers represented by formula (I), (II), (IIA), (IIB), (I-2), or (II-2) according to the present invention, are shown below, but the present invention should not be construed to be limited to them. Further, tautomers which have the hydrogen atom moved onto a nitrogen atom of the Cxe2x95x90N moiety, which is bonded at the coupling site (in which the hydrogen atom at the coupling site is moved onto the nitrogen at the Cxe2x95x90N moiety bonded to the coupling site), are also included in the present invention. 
In the following explanation, when the exemplified compounds (herein also referred to as a dye-forming coupler) shown above are referred to, the number X in the parenthesis, i.e., (X), is labeled to each of the exemplified compounds, and they are expressed as xe2x80x9ccoupler (X)xe2x80x9d.
Specific Synthetic Examples of the compounds represented by the foregoing formula (I) are described below.